What I Did for Prada

If you’re going to do whatever it takes to make it to the top, the least you deserve is an expensive pair of Italian high-heel open-toe shoes.

I will admit it: There have been times when I have undermined women in the workplace.

Early in my career, I learned the rush of being the only woman in a meeting. When I started in the CD-ROM business, working with rock groups, I wore jeans and a T-shirt to trick the men into thinking I was one of them. Then I realized that I was benefiting from being the only woman: My voice stood out. My point of view stood out. My legs stood out if I wore skirts, so I did.

As the CD-ROM industry blossomed into something totally inappropriate for the music industry, I sat in meeting after meeting with tables full of men. And I made enough money to buy some Prada shoes for New Year’s Eve.

When the Internet came, I doubled the male-to-me ratio — and I doubled my salary.

And then I did what all Internet professionals do when they double their salaries in six months: change jobs to do it again.

At my new company I built my team from scratch. And I found myself hiring a lot of women, but then, one day I stopped. I stopped hiring women because I thought I’d look less powerful to other people in the company if I ran a department full of women. Instead, I ran an affirmative-action program for tall, good-looking men. The interviews went on forever because phone screening for good looks had bad results, and I ended up scheduling interviews for everyone who applied. You might think this would make for an ineffective team, but not on the Internet: In six months, I doubled my salary.

Now, 10 pairs of Prada shoes later, I am at the semi-top of a semi-large Internet company, and I am being groomed to take over. As a COO who has ripped through the corporate ranks at Internet speed, my business-etiquette skills are about five bonus plans behind my operations and planning skills. For example, I go out for lunch and order coffee and dessert instead of a main course so I don’t fall asleep during the non-business part of the conversation.

My boss comes from a time when etiquette was everything and secretaries did all the work. I know this because he has two lunch dates every day with people whose names I see in Newsweek, and his secretary opens his Excel files because he doesn’t know how. My boss accompanied me to a convention where he made deals and I practiced approaching people I didn’t know, but mostly I just ate a lot of pastries. My boss took a break from his amazingly fluid networking to tell me that there are companies trying to talk to him about sequences and he told everyone that he’d send me over.

“Sequel,” I said. “Not sequences.”

“Whatever,” he said. “I don’t know that Internet stuff.”

He also stopped by the pastry table to tell me that we would be sitting at separate lunch tables.

I told him, “I’m already full.”

He told me, “You need to learn how to leverage a power lunch.”

My boss gave me some tips: “Ask people about themselves. People like to talk about themselves. Figure out why they’ll be interested in your company. Be a good listener.”

I told myself this was a good opportunity. My boss was trying to help me. I told myself I would never be able to run my own company until I could be the dealmaker that he was. I asked him how he decides where to sit when he walks into a room.

He said he looks for a chair next to a good-looking woman. He said it’s not that he wants to seduce her or anything; he just knows that women think he’s cute, so they’ll be most likely to talk to him. And besides, my boss said, men look better next to good-looking women.

My jaw dropped. I gathered thoughts for a speech on respect in the workplace. I weighed the idea of focusing on his insecurities to heighten my points. Then I remembered the all-male fiefdoms I’ve built during my Internet life. My jaw closed. Then it opened again when I said, “If there were a seat next to me, would you take it?”

Deborah Swan is a former health-care professional and long-time contributor at DLandroid24. Her industry knowledge and experience provide value. As an entrepreneur she knows what it takes to get businesses to the next level. She quit her career an started her own business.